Disazo dyestuffs containing A-O-alkylene-O-SO3 H group

ABSTRACT

Disazo dyestuffs of formula ##STR1## in which A represents an alkylene radical with 2 - 5 C atoms, 
     R 1 , r 2 , r 3  and R 5  represent hydrogen, chlorine, bromine, an alkoxy group or an alkyl group, 
     R 4  represents hydrogen, chlorine, bromine, alkyl, alkoxy or acylamino, 
     R 6  represents an alkyl group, 
     R 7  represents hydrogen or an alkyl group, 
     B represents a 1,4-phenylene or 1,4-naphthylene radical and 
     m represents the numbers 1 - 4, 
     And their use for the dyeing of nitrogen-containing materials, such as wool and silk, but preferably for dyeing synthetic polyamide and polyurethane fibres. Dyeings obtained are characterized by good to very good general fastness properties.

The subject of the invention are new disazo dyestuffs, containing sulphonic acid groups, of formula ##STR2## in which

A represents an alkylene radical with 2 - 5 C atoms,

R₁, R₂, R₃ and R₅ represents hydrogen, chlorine, bromine, an alkoxy group or an alkyl group,

R₄ represents hydrogen, chlorine, bromine, alkyl, alkoxy or acylamino,

R₆ represents an alkyl group,

R₇ represents hydrogen or an alkyl group,

B represents a 1,4-phenylene or 1,4-naphthylene radical and

M REPRESENTS THE NUMBERS 1 - 4, AS WELL AS THEIR MANUFACTURE AND USE FOR DYEING NITROGEN-CONTAINING FIBRE MATERIALS.

Preferred dyestuffs are here those of formula ##STR3## in which

A represents an alkylene radical with 2 - 5 C atoms,

R₁, R₂, R₃ and R₅ represent hydrogen, chlorine, bromine, an alkoxy group or an alkyl group,

R₄ represents hydrogen, chlorine, bromine, alkyl, alkoxy or acylamino,

R₆ represents an alkyl group,

B represents a 1,4-phenylene or 1,4-naphthylene radical and

M REPRESENTS THE NUMBERS 1 - 4, AS WELL AS THOSE OF FORMULA ##STR4## in which

R₉ represents hydrogen, hydroxyl, nitrile, halogen, alkoxycarbonyl, or

R₁ - R₅ as well as m have the abovementioned meaning, and also those of formula ##STR5## in which

R₁ ' represents hydrogen, chlorine or a methyl group,

R₂ ' represents hydrogen, chlorine, or a methyl or methoxy group,

R₃ ' represents hydrogen or a methoxy group,

R₄ ' represents hydrogen, chlorine, a methyl group or a formylamino, acetylamino, hydroxyacetylamino, benzoylamino, methoxycarbonylamino or ethoxycarbonylamino, benzenesulphonylamino, toluenesulphonylamino or a methylsulphonylamino or ethylsulphonylamino radical,

R₅ ' represents hydrogen or a methyl or methoxy group and

m represents the numbers 1 or 2, and also those of formula ##STR6## in which

R₁ represents hydrogen, chlorine, bromine, or a methyl, ethyl, methoxy or ethoxy group,

R₂ and R₃ independently of one another represent hydrogen, chlorine, bromine, or a methyl, ethyl, methoxy, or ethoxy group,

R₄ represents hydrogen, chlorine, bromine, a methyl, ethyl, methoxy or ethoxy group of a formylamino, acetylamine, propionylamino or hydroxyacetylamine group,

R₅ represents hydrogen or a methyl, methoxy or ethoxy group,

R₁₀ represents hydrogen, hydroxyl, lower alkylcarbonyloxy such as methylcarbonyloxy or ethylcarbonyloxy, lower alkoxycarbonyloxy such as methoxycarbonyloxy or ethoxycarbonyloxy, nitrile, halogen and alkoxycarbonyl, such as methoxycarbonyl or ethoxycarbonyl, alk represents alkyl radical with 1 - 4 C atoms, such as ##STR7## and

m represents an integer from 1 - 4, and also those of formula ##STR8## in which

R'₂ represents hydrogen or a methyl group,

R'₄ represents hydrogen, a methyl group or an acetylamino group,

R'₅ represents hydrogen or a methyl, methoxy or ethoxy group and

R'₁₀ represents hydrogen, chlorine, nitrile, an acetoxy- or a methoxycarbonyloxy group.

Suitable alkyl and alkoxy groups R₁ - R₇ are especially those with 1 - 4 C atoms. These radicals can possess further substituents, such as chlorine, hydroxyl, nitrile and the like.

The radicals R₁ can be identical or different.

Suitable radicals A are for example: ##STR9##

Suitable radicals B are above all radicals of formula ##STR10## in which

R₂ and R₃ have the abovementioned meaning.

Suitable alkyl radicals R₆ and R₇ are, for example, alkyl groups with 1 - 4 C atoms which are optionally substituted by hydroxyl, nitrile, halogen, alkoxycarbonyl or acyloxy groups, with possible alkoxycarbonyl groups being especially those with 1 - 4 C atoms in the alkoxy group, possible halogen being especially chlorine and bromine and possible acyloxy groups being especially alkylcarbonyloxy, arylcarbonyloxy and alkoxycarbonyloxy groups with 1 - 4 C atoms in the alkyl or alkoxy group.

Suitable optionally substituted alkyl groups R₆ and R₇ are here especially those of formula

    --Alk--R.sub.8

in which

Alk represents ##STR11##

R₈ denotes hydrogen or one of the abovementioned substituents.

Suitable acylamino groups are for example formylamino, alkylcarbonylamino, arylcarbonylamino, alkylsulphonylamino, arylsulphonylamino, alkoxycarbonylamino, and aminocarbonylamino groups, especially those with 1 - 4 C atoms in the alkyl or alkoxy group, such as acetylamino, hydroxyacetylamino, cyanacetylamino, propionylamino, methylsulphonylamino, ethylsulphonylamino, phenylsulphonylamino, methoxycarbonylamino, ethoxycarbonylamino and benzoylamino groups.

The new disazo dyestuffs (I) are manufactured by diazotising amines of formula ##STR12## in which

R₁, m and A have the abovementioned meaning, and reacting them with amines of formula ##STR13## in which

R₂, R₃ and B have the abovementioned meaning and

Z represents H, --SO₃ H or --CH₂ SO₃ H, to give monoazo dyestuffs of formula ##STR14## diazotising the monoazo dyestuffs thus obtained, after splitting off the group Z, if necessary, by alkaline or acid saponification, and coupling with an amine of formula ##STR15## in which

R₄ to R₇ have the abovementioned meaning.

A further process for the manufacture of the dyestuffs (I) consists of diazotising amines of formula ##STR16## in which

A, R₁ and m have the abovementioned meaning, and coupling them with amines of formula (VIII) to give monoazo dyestuffs of formula ##STR17## diazotising after splitting off the radical Z by acid or alkaline saponification, coupling with an amine of formula (X), and subsequently converting the disazo dyestuffs thus obtained, of formula ##STR18## in which

R₁ - R₇, A, B and m have the abovementioned meaning, into the dyestuffs (I) by means of sulphonating agents such as concentrated sulphuric acid, sulphuric acid monohydrate or oleum.

A further variant of the process according to the invention for the manufacture of the disazo dyestuffs (I) consists of converting the monoazo dyestuffs of formula (XII) into the dyestuffs of formula (IX) by means of sulphonating agents such as concentrated sulphuric acid, sulphuric acid monohydrate or oleum, diazotising, and coupling with amines of formula (X).

Suitable amines of formula (XI) are, for example: ethylene glycol-(4-aminophenyl)-ether, trimethylene glycol-(4-aminophenyl)-ether, propylene glycol-(4-aminophenyl)-ether, ethylene glycol-(2-methyl-4-aminophenyl)-ether, trimethylene glycol-(2-methyl-4-aminophenyl)-ether, propylene glycol-(2-methyl-4-aminophenyl)-ether, ethylene glycol-(3-methyl-4-aminophenyl)-ether, trimethylene glycol-(3-methyl-4-aminophenyl)-ether, ethylene glycol-(2-ethyl-4-aminophenyl)-ether, ethylene glycol-(3-ethyl-4-aminophenyl)-ether, trimethylene glycol-(3-ethyl-4-aminophenyl)-ether, ethylene glycol-(2-methoxy-4-aminophenyl)-ether, trimethylene glycol-(2-methoxy-4-aminophenyl)-ether, ethylene glycol-(3-methoxy-4-aminophenyl)-ether, trimethylene glycol-(3-methoxy-4-aminophenyl)-ether, ethylene glycol-(2-ethoxy-4-aminophenyl)-ether, ethylene glycol-(3-ethoxy-4-aminophenyl)-ether, ethylene glycol-(2-chlor-4-aminophenyl)-ether, trimethylene glycol-(2-chlor-4-aminophenyl)-ether, propylene glycol-(2-chlor-4-aminophenyl)-ether, ethylene glycol-(3-chlor-4-aminophenyl)-ether, trimethylene glycol-(3-chlor-4-aminophenyl)-ether, ethylene glycol-(2-brom- 4-aminophenyl)-ether, ethylene glycol-(3-brom-4-aminophenyl)-ether, ethylene glycol-(2,5-dimethyl-4-aminophenyl)-ether, trimethylene glycol-(2,6-dimethyl-4-aminophenyl)-ether, ethylene glycol-(2,6-dimethyl-4-aminophenyl)-ether, trimethylene glycol-(2,6-dimethyl-4aminophenyl)-ether, ethylene glycol-(2,3-dimethyl-4-aminopheny)-ether, ethylene glycol-(3,5-dimethyl-4-aminophenyl)-ether, ethylene glycol-(2,3,5-trimethyl-4-aminophenyl)-ether, trimethylene glycol-(2,3,5-trimethyl-4-aminophenyl)-ether, ethylene glycol-(2,3,5,6-tetramethyl-4-aminophenyl)-ether, ethylene glycol-(2,5-dichlor-4-aminophenyl)-ether, ethylene glycol-(2,6-dichlor-4-aminophenyl)-ether, trimethylene glycol-(2,6-dichlor-4-aminophenyl)-ether, ethylene glycol-(2-chlor-4-amino-5-methoxyphenyl)-ether, trimethylene glycol-(2-chlor-4-amino-5-methylphenyl)-ether and their acid sulphuric acid esters.

Suitable middle components of formula (VIII) are for example: aniline, 2-aminotoluene, 3-aminotoluene, 2-amino-ethylbenzene, 3-amino-ethylbenzene, 3-chloraniline, 3-bromaniline, 2-aminoanisole, 3-aminoanisole, 2-amino-ethoxybenzene, 3-amino-ethoxybenzene, 1-amino-2,3-dimethylbenzene, 1-amino-2,5-dimethylbenzene, 1-amino-3,5-dimethylbenzene, 3-amino-4-methoxy-toluene, 2-amino-4-methoxy-toluene, 2-amino-1,4-dimethoxy-benzene, 2-amino-4-ethoxy-toluene, 2-amino-1,4-diethoxy-benzene, α-naphthylamine and their N-sulphonic acid or N-Ω-methanesulphonic acids.

Suitable end components of formula (X) are, for example: N-methyl-aniline, N-ethyl-aniline, N-n-butyl-aniline, N-β-cyanethyl-aniline, N-β-chlorethyl-aniline, n-β-hydroxyethyl-aniline, N-β-acetoxyethyl-aniline, N-β-methoxy- and N-β-ethoxycarbonyloxyethyl-aniline, N-β-carbomethoxyethyl-aniline, N-β-cyanethyl-2-methyl-aniline, N-methyl-m-toluidine, N-ethyl-m-toluidine, N-β-cyanethyl-m-toluidine, N-β-chlorethyl-m-toluidine, N-β-hydroxyethyl-m-toluidine, N-β-acetoxyethyl-m-toluidine, Nβ-methoxycarbonyloxyethyl-m-toluidine, N-ethyl-3-ethyl-aniline, N-n-propyl-3-ethyl-aniline, N-β-cyanethyl-3-ethyl-aniline, N-β-cyanethyl-3-methoxy-aniline, N-β-chlorethyl-3-methoxy-aniline, N-β-cyanethyl-3-ethoxy-aniline, N-β-chlorethyl-3-ethoxy-aniline, N-ethyl-3-chlor-aniline, N-β-cyanethyl-3-chlor-aniline, N-β-chlorethyl-3-chlor-aniline, N-β-hydroxyethyl-3-chlor-aniline, N-β-acetoxyethyl-3-chlor-aniline, N-β-cyanethyl-3-brom-aniline, N-ethyl-N'-formyl-m-phenylenediamine, N-ethyl-N'-acetyl-m-phenylenediamine, N-β-cyanethyl-N'-formyl-m-phenylenediamine, N-β-cyanethyl-N'-acetyl-m-phenylenediamine, N-β-cyanethyl-N'-hydroxyacetyl-m-phenylenediamine, N-β-cyanethyl-N'-propionyl-m-phenylenediamine, N-β-cyanethyl-N'-benzoyl-m-phenylenediamine, N-β-cyanethyl-N'-methoxycarbonyl-m-phenylenediamine, N-β-cyanethyl-N'-ethoxy carbonyl-m-phenylenediamine, N-β-cyanethyl-N'-benzenesulphonyl-m-phenylenediamine, N-β-cyanethyl-N'-toluenesulphonyl-m-phenylenediamine, N-β-cyanethyl-N'-methylsulphonyl-m-phenylenediamine, N-β-cyanethyl-N'-ethylsulphonyl-m-phenylenediamine, N-β-chlorethyl-N'-acetyl-m-phenylenediamine, N-β-hydroxyethyl-N'-acetyl-m-phenylenediamine, N-β-acetoxyethyl-N'-acetyl-m-phenylenediamine, N-β-methoxycarbonyloxyethyl-N'-acetyl-m-phenylenediamine, N-β-carbomethoxyethyl-N'-acetyl-m-phenylenediamine, N-ethyl-2-methoxy-5-methyl-aniline, N-β-cyanethyl-2-methoxy-5-methyl-aniline, N-β-cyanethyl-2-ethoxy-5-methyl-aniline, N-β-cyanethyl-2,5-dimethyl-aniline, N-ethyl-2-methoxy-5-acetylamino-aniline, N-β-chlorethyl-2-methoxy-5-acetylamino- aniline, N-β-cyanethyl-2-methoxy-5-acetylamino-aniline, N-β-cyanethyl-2-ethoxy-5-acetylamino-aniline, N-β-cyanethyl-2-methoxy-5-formylamino-aniline, N-β-cyanethyl-2-methoxy-5-hydroxyacetylamino-aniline, N-β-cyanethyl-2-methoxy-5-propionylamino-aniline, N-β-cyanethyl-2-ethoxy-5-propionylamino-aniline, N-β-cyanethyl-2-ethoxy-5-hydroxyacetylamino-aniline, N-β-cyanethyl-2-methoxy-5-benzoylamino-aniline, N-β-cyanethyl-2-methoxy-5-methoxycarbonylamino-aniline, N-β-cyanethyl-2-methoxy-5-ethoxycarbonylamino-aniline, N-β-cyanethyl-2-methoxy-5-methylsulphonylamino-aniline, N-β-cyanethyl-2-methoxy-5-ethylsulphonylamino-aniline, N-β-hydroxyethyl-2-methoxy-5-acetylamino-aniline, N-β-acetoxyethyl-2-methoxy-5-acetylamino-aniline, N-β-methoxycarbonyloxyethyl-2-methoxy-5-acetylamino-aniline and N-β-cyanethyl-2-methyl-5-acetylamino-aniline.

N,N-Dimethylaniline, N,N-diethylaniline, N-methyl-N-n-butyl-aniline, N,N-diethyl-m-toluidine, N,N-diethylamino-3-chlorobenzene, N,N-diethyl-N'-formyl-m-phenylenediamine, N,N-diethyl-N'-acetyl-m-phenylenediamine, N,N-diethyl-N'-3-propionyl-m-phenylenediamine, N,N-diethylamine-3-methoxybenzene, 1-N,N-diethylamino-2,5-dimethoxybenzene, 1-N,N-diethylamino-2,5-diethoxybenzene, 1-N,N-diethylamino-2-methoxy-3-acetylamino-benzene, N-ethyl-N-β-chlorethyl-aniline, N,N-bis-(β-chlorethyl)-aniline, N-(β-chlorethyl)-N-butyl- aniline, N-(β-chlorethyl)-N-ethyl-m-toluidine, N,N-bis-(β-chlorethyl)-m-toluidine, N-methyl-N-β-hydroxyethyl-aniline, N-ethyl-N-β-hydroxyethyl-aniline, N,N-bis-(β-hydroxyethyl)-aniline, N-butyl-N-(β-hydroxyethyl)-aniline, N,N-bis(β,γ-dihydroxypropyl)-aniline, N-ethyl-N-β-hydroxyethyl-m-toluidine, N,N-bis-(β-hydroxyethyl)-m-toluidine, 1-N-ethyl-N-β-hydroxy-ethylamino-2-methoxy-5-methylbenzene, N-ethyl-N-β-hydroxyethyl-N'-acetyl-m-phenylenediamine, N,N-bis-(β-hydroxyethyl)-N'-acetyl-m-phenylenediamine, 1-N,N-bis-(β-hydroxyethyl)-amino-2-methoxy-5-acetylamino-benzene, 1-N,N-bis-(β-hydroxyethyl)-amino-2-ethoxy-5-acetylamino-benzene, 1-N,N-bis-(β-hydroxyethyl)-amino-2-methoxy-5-propionylamino-benzene, N-ethyl-N-β-acetoxyethylaniline, N,N-bis-(β-acetoxyethyl)-aniline, N-butyl-N-β-acetoxyethylaniline, N-ethyl-N-β-acetoxyethyl-m-toluidine, N,N-bis-(β-acetoxyethyl)-m-toluidine, 1-N-ethyl-N-β-acetoxyethylamino-2-methoxy-5-methylbenzene, N-ethyl-N-β-acetoxyethyl-N'-acetyl-m-phenylenediamine, N,N-bis-(β-acetoxyethyl)-N'-acetyl-m-phenylenediamine, 1-N,N-bis-(β-acetoxyethyl)-amino-2-methoxy-5-acetylamino-benzene, 1-N,N-bis-(β-acetoxyethyl)-amino-2-ethoxy-5-acetylamino-benzene, 1-N,N-bis-(β-acetoxyethyl)-amino-2-methoxy-5-propionyl-amino-benzene, N,N-bis-(β-ethoxycarbonyloxyethyl)-aniline, N,N-bis-(β-methoxycarbonyloxyethyl)-aniline, N,N-bis-(β-ethoxycarbonyloxyethyl)-m-toluidine, N,N-bis-(β-methoxy-carbonyloxyethyl)-m-toluidine, N,N-bis-(β-ethoxycarbonyloxyethyl)-N'-acetyl-m-phenylenediamine, N,N-bis-(β-methoxycarbonyloxyethyl)-N'-acetyl-m-phenylenediamine, 1-N,N-bis-(β-ethoxycarbonyloxyethyl)-amino-2-methoxy-5-acetylaminobenzene, 1-N,N-bis-(β-methoxycarbonyloxyethyl)-amino-2-methoxy-5-acetylaminobenzene, 1-N,N-bis-(β-ethoxycarbonyloxyethyl)-amino-2-ethoxy-5 -acetylaminobenzene, 1-N,N-bis-(β-methoxycarbonyloxyethyl)-amino-2-ethoxy-5-acetylaminobenzene, N,N-bis-(β-carbomethoxyethyl)-N'-acetyl-m-phenylenediamine, N-methyl-N-β-cyanethylaniline, N,N-bis-(β-cyanethyl)-aniline, N-ethyl-N-β-cyanethyl-m-toluidine, N-ethyl-N-β-cyanethyl-N'-acetyl-m-phenylenediamine, N-β-hydroxyethyl-N-β-cyanethylaniline, N-β-acetoxyethyl-N-β-cyanethyl-m-toluidine and N-β-methoxycarbonyloxyethyl-N-β-cyanethyl-N'-acetyl-m-phenylenediamine.

The diazo components of formula (VII) as well as of formula (XI) are diazotised in a manner which is in itself known, for example in acid, aqueous solution with sodium nitrite solution at 0°-20° C., and are combined with the coupling components of formula (VIII). The coupling can be performed in neutral to strongly acid, but preferably in a weakly acid, pH range, in an aqueous or aqueous-organic medium.

The monoazo dyestuffs formed can be isolated either directly on the basis of their insolubility in water, if diazo components of formula (XI) and coupling components of formula (VIII) with Z = H are employed, or by salting out if diazo components of formulae (VII) or (XI) and coupling components of formula (VIII) with Z = SO₃ H or --CH₂ SO₃ H are employed. In general, isolation of the monoazo dyestuff is, in the latter case, only necessary after the amino group of the coupling component has been liberated by alkaline or acid saponification. If diazo components of formula (VII) and coupling components of formula (VIII) with Z = SO₃ H or --CH₂ SO₃ H have been employed, an alkaline treatment to liberate the amino group of the coupling component is preferred, since the acid sulphuric acid ester is stable under these conditions. An intermediate isolation of the monoazo dyestuffs is however not always necessary -- they can also be diazotised further without isolation.

The further diazotisation of the aminoazo dyestuffs (IX) and (XII) with Z = H can for example be carried out in acid, aqueous dispersion with sodium nitrite solution, and the diazotisation temperatures can be between 0° and 30° C. Aminoazo dyestuffs of formula (IX) with Z = H can furthermore also be diazotised indirectly, by dissolving them in alkali, mixing with sodium nitrite solution and pouring into aqueous hydrochloric acid or mixing with hydrochloric acid. The conversion of the aminoazo dyestuff (XII) with Z = H, into the acid sulphuric acid ester can be performed by introducing (XII) into concentrated sulphuric acid, sulphuric acid monohydrate or oleum at room temperature and stirring for several hours longer. The acid sulphuric acid ester of the dyestuff can then be precipitated by introduction into ice water and isolated, or can also be further processed by direct further diazotisation.

The coupling of the diazotised aminoazo dyestuff (IX) with Z = H with the end components (X) to the disazo dyestuffs (I) also takes place in a manner which is in itself known, for example in a neutral, weakly acid or strongly acid aqueous medium or in an aqueous-organic medium. The disazo dyestuffs of formula (I) are generally rather sparingly soluble in an acid medium and can be isolated by simply filtering off, where necessary after addition of 2 - 10% of sodium chloride. If the dyestuffs are obtained in an impure form, they can be recrystallised in a known manner from hot water, with the addition of alkali where appropriate. The more sparingly soluble dyestuffs (I) isolated under acid conditions can be made easily water-soluble by mixing them with salts of strong bases and weak acids, for example trisodium phosphate, disodium hydrogen phosphate, sodium tetraborate, sodium metaphosphate, sodium metasilicate or sodium carbonate.

The coupling of the diazotised aminoazo dyestuffs (XII) with the end components (X) to the disazo dyestuffs (XIII) also takes place in a manner which is in itself known, for example in a neutral, weakly acid or strongly acid aqueous medium or in an aqueous-organic medium. The water-insoluble disazo dyestuffs (XIII) can be easily isolated by filtration. After drying, they are converted into the disazo dyestuffs (I) by introduction into concentrated sulphuric acid, sulphuric acid monohydrate or oleum and stirring for several hours longer, and these disazo dyestuffs are isolated by precipitation in ice water and filtration, and are freed of adhering sulphuric acid by subsequent washing with water or dilute alkalis.

The dyestuffs of formula (I) are suitable for dyeing nitrogen-containing materials, such as wool and silk, but preferably for dyeing synthetic polyamide and polyurethane fibres, in orange, scarlet red, bluish-tinged red, ruby and bordeaux shades having good to very good general fastness properties. The dystuffs are very well absorbed on polyamide fibres both from acid and from neutral dye baths.

In the examples which follow, parts denote parts by weight and percentages denote percentages by weight.

EXAMPLE 1

23.3 parts of the acid sulphuric acid ester of ethylene glycol-(4-aminophenyl)-ether are diazotised in aqueous solution, containing hydrochloric acid, in a known manner, and are coupled with 22 parts of m-toluidinemethanesulphonic acid at pH 3 - 3.5. After completion of coupling, the coupling solution is mixed with 4% strength sodium hydroxide solution, and heated to the boil for 11/2 to 2 hours, to split off the methanesulphonic acid radical. The aminoazo dyestuff thus formed is precipitated by neutralisation with hydrochloric acid at pH 7.5, with the separation being completed by mixing with 15% of sodium chloride, and is isolated. The monoazo dyestuff is again stirred with 300 parts of water and 30 parts of concentrated hydrochloric acid and is thereafter further diazotised with 6.9 parts of sodium nitrite (as a 30% strength aqueous solution) at 25° - 30° C. The suspension of the diazonium salt is thereafter run into a solution of 21.5 parts of N-β-cyanethyl-N'-acetyl-m-phenylenediamine in 200 parts of dilute hydrochloric acid, adjusted to pH 3.5 with sodium acetate. During the coupling, the pH value is kept at pH 3.5 with sodium acetate. After completion of the coupling, 10% of sodium chloride are added, and the dyestuff of formula ##STR19## which has separated out is isolated by filtration and is dried. 55 parts of a red dyestuff powder are obtained.

DYEING EXAMPLE

0.1 g of the dyestuff is dissolved hot in 100 ml of water, 5 ml of 10% strength ammonium acetate solution are added and the mixture diluted to a volume of 500 ml with water. 10 g of polyamide fibre are introduced into the dye bath, the dye bath is brought to the boil over the course of 20 minutes, 4 ml of 10% strength acetic acid are added and the system maintained at the boil for one hour. Thereafter the goods are rinsed and dried at 70° - 80° C. The polyamide material, dyed in a clear scarlet shade, shows very good general fastness properties.

An equivalent dyeing is obtained if no acetic acid is added to the dye bath.

If instead of polyamide fibres the same amount of wool fibres are employed and in other respects the procedure described in the preceding dyeing example is followed, a clear scarlet with similar good fastness properties is obtained on this material also.

EXAMPLE 2

Following the method described in example 1, 24.7 parts of the acid sulphuric acid ester of trimethylene glycol-(4-aminophenyl)-ether are diazotised, coupled to m-toluidinemethanesulphonic acid, the methanesulphonic acid radical split off, and the product further diazotised and coupled to 21.5 parts of N-β-cyanethyl-N'-acetyl-m-phenylenediamine. After completion of coupling, the dyestuff of formula ##STR20## is filtered off and dried. 56 parts of a red dyestuff powder, which dyes polyamide filaments in clear scarlet shades of good to very good fastness properties, are obtained.

EXAMPLE 3

Following the method described in example 1, 23.3 parts of the acid sulphuric acid ester of ethylene glycol-(4-aminophenyl)-ether are diazotised, coupled to m-toluidinemethanesulphonic acid, the methanesulphonic acid radical then split off and the product diazotised further. The suspension of the diazonium salt is thereafter run into a solution of 23 parts of N-β-cyanethyl-2 -methyl-5-acetylamino-aniline in approx. 200 parts of dilute hydrochloric acid adjusted to pH 3.5 with sodium acetate, with the pH value of the coupling solution being kept at pH 3.5 by adding sodium acetate solution. After completion of coupling, approx. 10% of sodium chloride are added and the dyestuff of formula ##STR21## which has separated out is isolated by filtration and dried. 53 parts of a red dyestuff powder, which dyes polyamide filaments in clear yellowish-tinged red shades having good to very good fastness properties, are obtained.

EXAMPLE 4

15.3 parts of ethylene glycol-(4-aminophenyl)-ether are diazotised in hydrochloric acid solution in a known manner, and coupled to 22 parts of m-toluidinemethanesulphonic acid in the manner described in example 1. After completion of coupling, the coupling solution is mixed with 4% strength sodium hydroxide solution and stirred for half an hour at 50° C. The monoazo dyestuff which has precipitated is filtered off, stirred with 300 parts of water and 30 parts of hydrochloric acid, and diazotised at 20° - 25° C. with 6.9 parts of sodium nitrite (as a 30% strength aqueous solution). The brown diazonium salt solution is filtered and added to a solution, adjusted to pH 2.5 - 3 with sodium acetate, of 15 parts of N-n-butyl aniline in approx. 200 parts of dilute hydrochloric acid, with the pH value of the coupling solution being kept at pH 3.5 - 4 by dropwise addition of sodium acetate solution. After completion of coupling, the dyestuff of formula ##STR22## is filtered off, dried and introduced over the course of approx. 30 minutes, at 20° - 25° C., into 300 parts of concentrated sulphuric acid. The sulphuric acid solution is stirred for a further 3 hours at room temperature and is then poured out onto sufficient ice for the temperature of the mixture not to rise above 10° C. The dyestuff which has precipitated, of formula ##STR23## is filtered off and washed copiously with water until free of acid. It dyes polyamide filaments in orange shades having good fastness properties.

EXAMPLE 5

15.3 parts of ethylene glycol-(4-aminophenyl)-ether are diazotised as described in example 4 and coupled at pH 3 - 3.5 to a solution of 14 parts of 3-amino-4-methoxy-toluene in approx. 200 parts of dilute hydrochloric acid, with the pH value of the coupling solution being kept at pH 3 - 3.5 by means of sodium acetate solution. After completion of coupling the aminoazo dyestuff is filtered off, dried and poured into 200 parts of concentrated sulphuric acid at 20° - 25° C. over the course of approx. 30 minutes. The mixture is stirred for a further 3 hours and poured out onto sufficient ice for the temperature of the mixture not to rise above 10° C. The precipitated dyestuff of formula ##STR24## is isolated, stirred with approx. 300 parts of water and 30 parts of concentrated hydrochloric acid and diazotised at 25° - 30° C. with 6.9 parts of sodium nitrite (as a 30% strength aqueous solution). The suspension of the diazonium salt is run into a solution of 25 parts of N-β-acetoxyethyl-N'-acetyl-m-phenylenediamine in approx. 200 parts of dilute hydrochloric acid, adjusted to pH 3 - 4 with sodium acetate, with the pH value of the coupling solution being kept at 3 - 4 by means of sodium acetate solution. After completion of coupling, approx. 5% of sodium chloride are added and the dyestuff of formula ##STR25## is filtered off and dried. 54 parts of a dark red powder, which dyes polyamide filaments in bluish-tinged red shades having good fastness properties, are obtained.

EXAMPLE 6

23.3 parts of the acid sulphuric acid ester of ethylene glycol-(4-aminophenyl)-ether are diazotised as described in example 1 and coupled to 14 parts of 3-amino-4-methoxy-toluene as described in example 5. After completion of coupling, the monoazo dyestuff is isolated and further diazotised as described in example 5. The suspension of the diazonium salt is run into a solution of 21.5 parts of N-β-cyanethyl-N'-acetyl-m-phenylenediamine in approx. 200 parts of dilute hydrochloric acid, adjusted to pH 3.5 by means of sodium acetate, with a pH value of 3.5 being maintained during coupling. After completion of coupling, the dyestuff of formula ##STR26## is isolated and dried. It dyes polyamide filaments in a bluish-tinged red having good to very good fastness properties.

EXAMPLE 7

26.75 parts of the acid sulphuric acid ester of ethylene glycol-(2-chlor-4-aminophenyl)-ether are diazotised in a known manner in an aqueous solution containing hydrochloric acid and, following the procedure described in example 5, coupled to 14 parts of 3-amino-4-methoxy-toluene, further diazotised and coupled to 21.5 parts of N-β-cyanethyl-N'-acetyl-m-phenylenediamine. The resulting dyestuff of formula ##STR27## dyes polyamide materials in clear, strongly bluish-tinged red shades having very good fastness properties.

EXAMPLE 8

Following the procedure described in example 7, 28.15 parts of the acid sulphuric acid ester of trimethylene glycol-(2-chlor-4-aminophenyl)-ether are diazotised, coupled to 14 parts of 3-amino-4-methoxy-toluene, further diazotised and coupled to 21.5 parts of N-β-cyanethyl-N'-acetyl-m-phenylene-diamine. The resulting dyestuff of formula ##STR28## dyes polyamide materials in clear, bluish-tinged red shades having very good fastness properties.

EXAMPLE 9

Following the procedure described in example 7, 28.15 parts of the acid sulphuric acid ester of propylene glycol-(2-chlor-4-aminophenyl)-ether are diazotised, coupled to 14 parts of 3-amino-4-methoxy-toluene, further diazotised and coupled to 21.5 parts of N-β-cyanethyl-N'-acetyl-m-phenylenediamine. The resulting dyestuff of formula ##STR29## dyes polyamide materials in clear, bluish-tinged red shades having very good fastness properties.

EXAMPLE 10

26.75 parts of the acid sulphuric acid ester of ethylene glycol-(3-chlor-4-aminophenyl)-ether are diazotised in the customary manner in an aqueous solution containing hydrochloric acid and, following the procedure described in example 1, coupled to 22 parts of m-toluidinemethanesulphonic acid, the methanesulphonic acid radical split off and the product further diazotised. The suspension of the diazonium salt is run into a solution of 23 parts of N-β-cyanethyl-N'-propionyl-m-phenylenediamine in approx. 200 parts of dilute hydrochloric acid, adjusted to pH 3.5 with sodium acetate, with the pH value of 3.5 being maintained during coupling by adding sodium acetate solution. After completion of coupling, the dyestuff of formula ##STR30## is isolated and dried. It represents a dark brown powder which dyes polyamide filaments in clear scarlet shades.

EXAMPLE 11

Following the procedure described in example 1, 30.2 parts of the acid sulphuric acid ester of ethylene glycol-(2,6-dichlor-4-aminophenyl)-ether are diazotised, coupled to m-toluidinemethanesulphonic acid, the methanesulphonic acid radical split off and the product further diazotised. The final coupling,, to 25 parts of N-β-cyanethyl-N'-methylsulphonyl-m-phenylenediamine, is carried out under the same conditions as described in example 1. After isolation, 58 parts of the dyestuff of formula ##STR31## which dyes polyamide filaments in clear ruby shades having good to very good fastness properties, are obtained.

EXAMPLE 12

Following the procedure described in example 1, 24.7 parts of the acid sulphuric acid ester of ethylene glycol-(3-methyl-4-aminophenyl)-ether are diazotised, coupled to 19.5 parts of anilinemethanesulphonic acid, the methanesulphonic acid radical split off and the product diazotised further. The final coupling, to 21.5 parts of N-β-cyanethyl-N'-acetyl-m-phenylenediamine, is carried out under the same conditions as described in example 1. After isolation, 51 parts of the dyestuff of formula ##STR32## which dyes polyamide filaments in clear yellowish-tinged red shades, are obtained.

EXAMPLE 13

23.3 parts of the acid sulphuric acid ester of ethylene glycol-(4-aminophenyl)-ether are diazotised as described in example 1 and coupled to an aqueous suspension of 18 parts of α-naphthylamine hydrochloride, buffered to pH 2 with sodium acetate, with the pH value being kept at pH 2 - 2.5 during the coupling. After completion of coupling, the monoazo dyestuff formed is isolated and diazotised in approx. 300 parts of ethylene glycol monoethyl ether and 30 parts of sodium nitrite (as a 30% strength aqueous solution). The brown diazonium salt suspension is thereafter allowed to run into a solution of 21.5 parts of N-β-cyanethyl-N'-acetyl-m-phenylenediamine in 200 parts of dilute hydrochloric acid, adjusted to pH 3.5 by means of sodium acetate. During coupling, the pH value is kept at pH 3.5 by means of sodium acetate. After completion of coupling, the dyestuff of formula ##STR33## which has separated out is isolated and dried. It dyes polyamide materials in clear ruby shades having good fastness properties.

If the procedure indicated in the preceding examples is followed, using the starting components, middle components and end components indicated in the Table which follows, disazo dyestuffs are obtained which dye polyamide in the indicated colour shades.

    __________________________________________________________________________                      Middle                 Shade on                               Starting component                                                                              component                                                                            End component    Polyamide                              __________________________________________________________________________     14   Acid sulphuric acid                                                                        aniline                                                                              N-methyl-aniline orange                                      ester of                                                                       ethylene glycol-                                                               (4-amino-phenyl)-ether                                                    15   "           aniline                                                                              N-ethyl-aniline  orange                                 16   "           aniline                                                                              N-n-propyl-aniline                                                                              orange                                 17   "           aniline                                                                              N-n-butyl-aniline                                                                               orange                                 18   "           aniline                                                                              N-β-chlorethyl-aniline                                                                     orange                                 19   "           aniline                                                                              N-β-cyanethyl-aniline                                                                      orange                                 20   "           aniline                                                                              N-β-hydroxyethyl-aniline                                                                   orange                                 21   "           aniline                                                                              N-ethyl-m-toluidine                                                                             orange                                 22   "           aniline                                                                              N-β-cyanethyl-m-toluidine                                                                  orange                                 23   "           aniline                                                                              N-β-acetoxyethyl-m-                                                                        orange                                                        toluidine                                               24   "           aniline                                                                              N-β-methoxycarbonyloxy-                                                                    orange                                                        ethyl-m-toluidine                                       25   "           aniline                                                                              N-β-cyanethyl-3-methoxy                                                                    orange                                                        aniline                                                 26   "           aniline                                                                              N-β-chlorethyl-3-chlor-                                                                    orange                                                        aniline                                                 27   "           aniline                                                                              N-β-cyanethyl-3-chlor-                                                                     orange                                                        aniline                                                 28   "           aniline                                                                              N-ethyl-N'-acetyl-m-                                                                            yellowish-tinged red                                          phenylenediamine                                        29   "           aniline                                                                              N-β-cyanethyl-N'-hydroxy-                                                                  yellowish-tinged red                                          acetyl-m-phenylenediamine                               30   "           aniline                                                                              N-β-cyanethyl-N'-acetyl-                                                                   yellowish-tinged red                                          m-penylenediamine                                       31   "           aniline                                                                              N-β-cyanethyl-N'-propionyl-                                                                yellowish-tinged red                                          m-phenylenediamine                                      32   "           aniline                                                                              N-β -cyanethyl-N'-benzoyl-                                                                 yellowish-tinged red                                          m-phenylenediamine                                      33   "           aniline                                                                              N-β-cyanethyl-N'-methyl-                                                                   yellowish-tinged red                                          sulphonyl-m-phenylenediamine                            34   "           aniline                                                                              N-β-cyanethyl-N'-ethyl-                                                                    yellowish-tinged red                                          sulphonyl-m-phenylene-                                                         diamine                                                 35   "           aniline                                                                              N-β-cyanethyl-N'-methoxy-                                                                  yellowish-tinged red                                          carbonyl-m-phenylenediamine                             36   "           aniline                                                                              N-β-cyanethyl-N'-ethoxy-                                                                   yellowish-tinged red                                          carbonyl-m-phenylenediamine                             37   "           aniline                                                                              N-β-methoxycarbonyloxy-                                                                    red                                                           ethyl-N'-acetyl-m-phenylene-                                                   diamine                                                 38   "           aniline                                                                              N-β-carbomethoxyethyl-N'-                                                                  red                                                           acetyl-m-phenylenediamine                               39   "           aniline                                                                              N-ethyl-2-methoxy-5-methyl-                                                                     orange                                                        aniline                                                 40   "           aniline                                                                              N-β-cyanethyl-2-methoxy-                                                                   orange                                                        5-methyl-aniline                                        41   "           aniline                                                                              N-β-cyanethyl-2-ethoxy-                                                                    orange                                                        5-methyl-aniline                                        42   "           aniline                                                                              N-β-cyanethyl-m-anisidine                                                                  orange                                 43   "           aniline                                                                              N-β-cyanethyl-3-ethyl-                                                                     orange                                                        aniline                                                 44   "           aniline                                                                              N-β-cyanethyl-3-ethoxy-                                                                    orange                                                        aniline                                                 45   "           aniline                                                                              N-β-cyanethyl-3-brom-                                                                      orange                                                        aniline                                                 46   "           aniline                                                                              N-β-cyanethyl-N'-benzene-                                                                  yellow-red                                                    sulphonyl-m-phenylenediamine                            47   "           aniline                                                                              N-βcyanethyl-2-methyl-5-                                                                   yellow-red                                                    acetylamino-aniline                                     48   "           aniline                                                                              N-β-cyanethyl-2-methoxy-                                                                   bluish-tinged red                                             5-acetylamino-aniline                                   49               aniline                                                                              N-β-carboethoxyethyl-                                                                      orange                                                        aniline                                                 50   "           m-toluidine                                                                          N-methyl-aniline orange                                 51   "           m-toluidine                                                                          N-n-propyl-aniline                                                                              orange                                 52   "           m-toluidine                                                                          N-i-propyl-aniline                                                                              orange                                 53   "           m-toluidine                                                                          N-i-butyl-aniline                                                                               orange                                 54   "           m-toluidine                                                                          N-β-cyanethyl-aniline                                                                      orange                                 55   "           m-toluidine                                                                          N-β-hydroxyethyl-aniline                                                                   orange                                 56   "           m-toluidine                                                                          N-β-chlorethyl-aniline                                                                     orange                                 57   "           m-toluidine                                                                          N-γ-hydroxypropyl-aniline                                                                 orange                                 58   "           m-toluidine                                                                          N-γ-chloropropyl-aniline                                                                  orange                                 59   "           m-toluidine                                                                          N-δ-chlorobutyl-aniline                                                                   orange                                 60   "           m-toluidine                                                                          N-β-acetoxyethyl-aniline                                                                   orange                                 61   "           m-toluidine                                                                          N-β-methoxycarbonyloxy-                                                                    orange                                                        ethyl-aniline                                           62   "           m-toluidine                                                                          N-β-ethoxycarbonyloxy-                                                                     orange                                                        ethyl-aniline                                           63   "           m-toluidine                                                                          N-β-carbomethoxyethyl-                                                                     orange                                                        aniline                                                 64   "           m-toluidine                                                                          N-β-carboeethoxyethyl-                                                                     orange                                                        aniline                                                 65   "           m-toluidine                                                                          N-methyl-m-toluidine                                                                            orange                                 66   "           m-toluidine                                                                          N-ethyl-m-toluidine                                                                             orange                                 67   "           m-toluidine                                                                          N-β-hydroxyethyl-m-                                                                        orange                                                        toluidine                                               68   "           m-toluidine                                                                          N-β-acetoxyethyl-m-                                                                        orange                                                        toludine                                                69   "           m-toluidine                                                                          N-β-methoxycarbonyloxy-                                                                    orange                                                        ethyl-m-toluidine                                       70   "           m-toluidine                                                                          N-β-ethoxycarbonyloxy-                                                                     orange                                                        ethyl-m-toluidine                                       71   "           m-toluidine                                                                          N-β-chlorethyl-m-toluidine                                                                 orange                                 72   "           m-toluidine                                                                          N-γ-chloropropyl-m-toluidine                                                              orange                                 73   "           m-toludine                                                                           N-β-cyanethyl-m-toluidine                                                                  orange                                 74   "           m-toluidine                                                                          N-ethyl-3-ethyl-aniline                                                                         orange                                 75   "           m-toluidine                                                                          N-β-hydroxyethyl-3-ethyl-                                                                  orange                                                        aniline                                                 76   "           m-toluidine                                                                          N-β-cyanethyl-3-ethyl-                                                                     orange                                                        aniline                                                 77   "           m-toluidine                                                                          N-ethyl-3-chlor-aniline                                                                         orange                                 78   "           m-toluidine                                                                          N-ethyl-3-brom-aniline                                                                          orange                                 79   "           m-toluidine                                                                          N-β-cyanethyl-3-chlor-                                                                     orange                                                        aniline                                                 80   "           m-toluidine                                                                          N-ethyl-m-anisidine                                                                             orange                                 81   "           m-toluidine                                                                          N-β-cyanethyl-m-anisidine                                                                  orange                                 82   "           m-toluidine                                                                          N-β-chlorethyl-m-anisidine                                                                 orange                                 83   "           m-toluidine                                                                          N-β-chlorethyl-3-chlor-                                                                    orange                                                        aniline                                                 84   "           m-toluidine                                                                          N-β-acetoxyethyl-3-chlor-                                                                  orange                                                        aniline                                                 85   "           m-toluidine                                                                          N-ethyl-3-ethoxy-aniline                                                                        orange                                 86   "           m-toluidine                                                                          N-β-cyanethyl-3-ethoxy-                                                                    orange                                                        aniline                                                 87   "           m-toluidine                                                                          N-ethyl-N'-formyl-m-                                                                            yellowish-tinged red                                          phenylenediamine                                        88   "           m-toluidine                                                                          N-ethyl-N'-acetyl-m-                                                                            yellowish-tinged red                                          phenylenediamine                                        89   "           m-toluidine                                                                          N-ethyl-N'-benzoyl-m-                                                                           yellowish-tinged red                                          phenylenediamine                                        90   "           m-toluidine                                                                          N-β-hydroxyethyl-N'-                                                                       yellowish-tinged red                                          acetyl-m-phenylenediamine                               91   "           m-toluidine                                                                          N-β-acetoxyethyl-N'-                                                                       yellowish-tinged red                                          acetyl-m-phenylenediamine                               92   "           m-toluidine                                                                          N-β-chlorethyl-N'-acetyl-                                                                  yellowish-tinged red                                          m-phenylenediamine                                      93   "           m-toluidine                                                                          N-β-cyanethyl-N'-formyl-                                                                   scarlet                                                       m-phenylenediamine                                      94   "           m-toluidine                                                                          N-β-cyanethyl-N'-hydroxy-                                                                  scarlet                                                       acetyl-m-phenylenediamine                               95   "           m-toluidine                                                                          N-β-cyanethyl-N'-propionyl-                                                                scarlet                                                       m-phenylenediamine                                      96   "           m-toluidine                                                                          N-β-cyanethyl-N'-benzoyl-                                                                  scarlet                                                       m-phenylenediamine                                      97   "           m-toluidine                                                                          N-β-cyanethyl-N'-methyl-                                                                   scarlet                                                       sulphonyl-m-phenylene-                                                         diamine                                                 98   "           m-toluidine                                                                          N-β-cyanethyl-N'-ethyl-                                                                    scarlet                                                       sulphonyl-m-phenylene-                                                         diamine                                                 99   "           m-toluidine                                                                          N-β-cyanethyl-N'-benzene-                                                                  scarlet                                                       sulphonyl-m-phenylenediamine                            100  "           m-toluidine                                                                          N-β-cyanethyl-N'-toluene-                                                                  scarlet                                                       sulphonyl-m-phenylenediamine                            101  "           m-toluidine                                                                          N-β-cyanethyl-N'-methoxy-                                                                  scarlet                                                       carbonyl-m-phenylenediamine                             102  "           m-toluidine                                                                          N-β-cyanethyl-N'-ethoxy-                                                                   scarlet                                                       carbonyl-m-phenylenediamine                             103  "           m-toluidine                                                                          N-β-carbomethyoxyethyl-N'-                                                                 scarlet                                                       acetyl-m-phenylenediamine                               104  "           m-toluidine                                                                          N-ethyl-2-methoxy-5-                                                                            yellowish-tinged red                                          methyl-aniline                                          105  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-                                                                   yellowish-tinged red                                          5-methyl-aniline                                        106  "           m-toluidine                                                                          N-β-hydroxyethyl-2-methoxy-                                                                yellowish-tinged red                                          5-methyl-aniline                                        107  "           m-toluidine                                                                          N-β-cyanethyl-2-ethoxy-5-                                                                  yellowish-tinged red                                          methyl-aniline                                          108  "           m-toluidine                                                                          N-β-cyanethyl-2,5-dimethyl-                                                                orange                                                        aniline                                                 109  "           m-toluidine                                                                          N-β-cyanethyl-2-ethyl-5-                                                                   bluish-tinged red                                             acetylamino-aniline                                     110  "           m-toluidine                                                                          N-ethyl-2-methoxy-5-                                                                            bluish-tinged red                                             acetylamino-aniline                                     111  "           m-toluidine                                                                          N-ethyl-2-ethoxy-5-                                                                             bluish-tinged red                                             acetylamino-aniline                                     112  "           m-toluidine                                                                          N-ethyl-2-methoxy-5-                                                                            bluish-tinged red                                             propionylamino-aniline                                  113  "           m-toluidine                                                                          N-n-butyl-2-methoxy-5-                                                                          bluish-tinged red                                             acetylamino-aniline                                     114  "           m-toluidine                                                                          N-β-hydroxyethyl-2-methoxy-                                                                bluish-tinged red                                             5-acetylamino-aniline                                   115  "           m-toluidine                                                                          N-β-acetoxyethyl-2-methoxy-                                                                bluish-tinged red                                             5-acetylamino-aniline                                   116  "           m-toluidine                                                                          N-β-methoxycarbonyloxy-                                                                    bluish-tinged red                                             ethyl-2-methoxy-5-acetyl-                                                      amino-aniline                                           117  "           m-toluidine                                                                          N-β-chlorethyl-2-methoxy-                                                                  bluish-tinged red                                             5-acetylamino-aniline                                   118  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             formylamino-aniline                                     119  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             acetylamino-aniline                                     120  "           m-toluidine                                                                          N-β-cyanethyl-2-ethoxy-5-                                                                  bluish-tinged red                                             acetylamino-aniline                                     121  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             hydroxyacetylamino-aniline                              122  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             propionylamino-aniline                                  123  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             benzoylamino-aniline                                    124  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             benzenesulphonyl-amino-                                                        aniline                                                 125  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             toluenesulphonylamino-                                                         aniline                                                 126  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             methylsulphonylamino-aniline                            127  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             ethylsulphonylamino-aniline                             128  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             methoxycarbonylamino-aniline                            129  "           m-toluidine                                                                          N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                             ethoxycarbonylamino-aniline                             130  "           3-amino-5-                                                                           N-ethyl-aniline  reddish-tinged orange                                   methoxy-                                                                       toluene                                                       131  "           3-amino-4-                                                                           N-β-cyanethyl-aniline                                                                      reddish-tinged orange                                   methoxy-                                                                       toluene                                                       132  "           3-amino-4-                                                                           N-β-hydroxyethyl-aniline                                                                   reddish-tinged orange                                   methoxy-                                                                       toluene                                                       133  "           3-amino-4-                                                                           N-β-cyanethyl-m-toluidine                                                                  reddish-tinged orange                                   methoxy-                                                                       toluene                                                       134  "           3-amino-4-                                                                           N-β-cyanethyl-3-chlor-aniline                                                              reddish-tinged orange                                   methoxy-                                                                       toluene                                                       135  "           3-amino-4-                                                                           N-β-cyanethyl-m-anisidine                                                                  reddish-tinged orange                                   methoxy-                                                                       toluene                                                       136  "           3-amino-4-                                                                           N-β-chlorethyl-m-anisidine                                                                 reddish-tinged orange                                   methoxy-                                                                       toluene                                                       137  "           3-amino-4-                                                                           N-ethyl-N'-acetyl-m-                                                                            bluish-tinged red                                       methoxy-                                                                             phenylenediamine                                                         toluene                                                       138  "           3-amino-4-                                                                           N-β-cyanethyl-N'-hydroxy-                                                                  bluish-tinged red                                       methoxy-                                                                             acetyl-m-phenylenediamine                                                toluene                                                       139  "           3-amino-4-                                                                           N-β-cyanethyl-N'-propionyl-                                                                bluish-tinged red                                       methoxy-                                                                             m-phenylenediamine                                                       toluene                                                       140  "           3-amino-4-                                                                           N-β-cyanethyl-N'-benzoyl-                                                                  bluish-tinged red                                       methoxy                                                                              m-phenylenediamine                                                       toluene                                                       141  "           3-amino-4-                                                                           N-β-cyanethyl-N'-benzene-                                                                  bluish-tinged red                                       methoxy-                                                                             sulphonyl-m-phenylenediamine                                             toluene                                                       142  "           3-amino-4-                                                                           N-β-cyanethyl-N'-methyl-                                                                   bluish-tinged red                                       methoxy-                                                                             sulphonyl-m-phenylenediamine                                             toluene                                                       143  "           3-amino-4-                                                                           N-β-cyanethyl-N'-methoxy-                                                                  bluish-tinged red                                       methoxy-                                                                             carbonyl-m-phenylenediamine                                              toluene                                                       144  "           3-amino-4-                                                                           N-β-cyanethyl-2-methoxy-5-                                                                 bluish-tinged red                                       methoxy-                                                                             methyl-aniline                                                           toluene                                                       145  "           3-amino-4-                                                                           N-β-cyanethyl-2-methyl-5-                                                                  bluish-tinged red                                       methoxy                                                                              acetylamino-aniline                                                      toluene                                                       146  "           3-amino-4-                                                                           N-β-chlorethyl-2-methoxy-                                                                  ruby                                                    methoxy-                                                                             5-acetylamino-aniline                                                    toluene                                                       147  "           3-amino-4-                                                                           N-β-cyanethyl-2-methoxy-5-                                                                 ruby                                                    methoxy-                                                                             formylamino-aniline                                                      toluene                                                       148  "           3-amino-4-                                                                           N-βcyanethyl-2-methoxy-                                                                    ruby                                                    methoxy-                                                                             5-acetylamino-aniline                                                    toluene                                                       149  "           3-amino-4-                                                                           N-β-cyanethyl-2-methoxy-                                                                   ruby                                                    methoxy-                                                                             5-propionylamino-aniline                                                 toluene                                                       150  "           3-amino-4-                                                                           N-β-cyanethyl-2-ethoxy-                                                                    ruby                                                          5-acetylamino-aniline                                   151  "           3-amino-4-                                                                           N-β-cyanethyl-2-methoxy-5-                                                                 ruby                                                    methoxy-                                                                             benzenesulphonylamino-aniline                                            toluene                                                       152  "           3-amino-4-                                                                           N-β-cyanethyl-2-methoxy-5-                                                                 ruby                                                    methoxy-                                                                             methoxycarbonylamino-aniline                                             toluene                                                       __________________________________________________________________________

EXAMPLE 153

Following the procedure described in example 1, 23.3 parts of the acid sulphuric acid ester of ethylene glycol-(4-aminophenyl)-ether are diazotised, coupled to m-toluidine-methanesulphonic acid, the methanesulphonic acid radical then split off, and the product further diazotised. The suspension of the diazonium salt is thereafter run into a solution of 18 parts of N-ethyl-N-β-cyanethylaniline in approx. 200 parts of dilute hydrochloric acid, adjusted to pH 3.5 by means of sodium acetate, with the pH value of the coupling solution being kept at pH 3.5 by addition of sodium acetate solution. After completion of coupling, approx. 5% of sodium chloride are added and the dyestuff which has separated out, of formula ##STR34## is isolated by filtration and dried. 45 parts of a light red dyestuff powder, which dyes polyamide filaments in clear orange shades having very good fastness properties, are obtained.

EXAMPLE 154

Following the procedure described in example 1, 26.75 parts of the acid sulphuric acid ester of ethylene glycol-(2-chlor-4-aminophenyl)- ether are diazotised, coupled to m-toluidinemethanesulphonic acid, the methanesulphonic acid radical split off, and the product diazotised further. The suspension of the diazonium salt is thereafter run into a solution of 35.4 parts of N,N-bis-(β-methoxycarbonyloxyethyl)-N'-acetyl-m-phenylenediamine in approx. 200 parts of dilute acetic acid and 50 parts of dimethylformamide, adjusted to pH 3.5 by means of sodium acetate. The pH value is kept at pH 3.5 - 4 during the coupling by addition of sodium acetate. After completion of the coupling, approx. 10% of sodium chloride are added and the dyestuff which has separated out, of formula ##STR35## is isolated and dried. 70 parts of a dark red dyestuff powder, which dyes polyamide filaments in red shades having good to very good fastness properties, are obtained.

EXAMPLE 155

24.7 parts of the acid sulphuric acid ester of ethylene glycol-(3-methyl-4-aminophenyl)-ether are diazotised in the usual manner, coupled to 19.5 parts of anilinemethanesulphonic acid, the methanesulphonic acid radical split off and the product diazotised further. The suspension of the diazonium salt is run into a solution of 23.7 parts of N,N-bis-(β-chlorethyl)-m-toluidine in approx. 200 parts of dilute acetic acid, adjusted to pH 3 - 4 by means of sodium acetate solution, with the pH value of 3 - 4 being maintained during the coupling by addition of sodium acetate solution. After completion of coupling, the dyestuff of formula ##STR36## is completely precipitated by adding 10% of sodium chloride, and isolated. It dyes polyamide filaments in clear orange shades having good fastness properties.

The Table which follows lists further dyestuffs obtained according to the invention, which dye polyamide filaments in the indicated shades:

    __________________________________________________________________________                       Middle                   Shade on                            Starting component                                                                               component                                                                              End component    Polyamide                           __________________________________________________________________________     156  Acid sulphuric acid                                                                         aniline N,N-diethylaniline                                                                              orange                                   ester of ethylene glycol-                                                      (4-aminophenyl)-ether                                                     157  "            aniline N,N-diethyl-m-toluidine                                                                         orange                              158  "            aniline N,N-diethyl-3-chlor-aniline                                                                     orange                              159  "            aniline N-ethyl-N-β-chlorethyl-aniline                                                             orange                              160  "            aniline N-ethyl-N-β-cyanethyl-aniline                                                              orange                              161  "            aniline N-butyl-N-β-cyanethyl-aniline                                                              orange                              162  "            aniline N-ethyl-N-β-cyanethyl-m-                                                                   orange                                                        toluidine                                            163  "            aniline N-ethyl-N-β-cyanethyl-3-                                                                   orange                                                        chlor-aniline                                        164  "            aniline N-ethyl-N-β-cyanethyl-3-                                                                   orange                                                        brom-aniline                                         165  "            aniline N,N-bis-(β-chlorethyl)-                                                                    orange                                                        aniline                                              166  "            aniline N-ethyl-N-β-hydroxyethyl-                                                                  orange                                                        aniline                                              167  "            aniline N-ethyl-N-β-acetoxyethyl-                                                                  orange                                                        aniline                                              168  "            aniline N-β-acetoxyethyl-N-β-                                                                 orange                                                        cyanethyl-aniline                                    169  "            aniline N-β-chlorethyl-N-β-cyanethyl-                                                         orange                                                        aniline                                              170  "            aniline N-bis-(β-hydroxyethyl)-                                                                    orange                                                        aniline                                              171  "            aniline N-bis-(β-acetoxyethyl)-                                                                    orange                                                        aniline                                              172  "            aniline N-bis-(β-methoxycarbonyl-                                                                  orange                                                        oxyethyl)-aniline                                    173  "            aniline N-bis-(β-carbomethoxyethyl)-                                                               orange                                                        aniline                                              174  "            aniline N-butyl-N-β-cyanethyl-m-                                                                   orange                                                        toluidine                                            175  "            aniline N-ethyl-N-β-chlorethyl-m-                                                                  orange                                                        toluidine                                            176  "            aniline N-ethyl-N-β-hydroxyethyl-m-                                                                orange                                                        toluidine                                            177  "            aniline N-ethyl-N-β-acetoxyethyl-m-                                                                orange                                                        toluidine                                            178  "            aniline N-ethyl-N-β-methoxycarbonyl-                                                               orange                                                        oxyethyl-m-toluidine                                 179  "            aniline N,N-bis-(β-chlorethyl)-m-                                                                  orange                                                        toluidine                                            180  "            aniline N,N-bis-(β-hydroxyethyl)-                                                                  orange                                                        m-toluidine                                          181  "            aniline N,N-bis(β-acetoxyethyl)-m-                                                                 orange                                                        toluidine                                            182  "            aniline N,N-bis-(β-methoxycarbonyloxy-                                                             orange                                                        ethyl)-m-toluidine                                   183  "            aniline N-ethyl-N-β-cyanethyl-3-                                                                   orange                                                        ethyl-aniline                                        184  "            aniline N-ethyl-N-β-hydroxyethyl-                                                                  orange                                                        3-ethyl-aniline                                      185  "            aniline N-ethyl-N-β-acetoxyethyl-                                                                  orange                                                        3-ethyl-aniline                                      186  "            aniline N-ethyl-N-β-acetoxyethyl-                                                                  orange                                                        3-chlor-aniline                                      187  "            aniline N-ethyl-N-β-cyanethyl-o-                                                                   orange                                                        toluidine                                            188  "            aniline N-ethyl-N-β-acetoxyethyl-                                                                  orange                                                        o-toluidine                                          189  "            aniline N,N-diethyl-m-anisidine                                                                         orange                              190  "            aniline N-ethyl-N-β-cyanethyl-m-                                                                   orange                                                        anisidine                                            191  "            aniline N,N-diethyl-2,5-dimethyl-                                                                       orange                                                        aniline                                              192  "            aniline N-ethyl-N-β-cyanethyl-                                                                     orange                                                        2,5-dimethyl-aniline                                 193  "            aniline N-ethyl-N-β-hydroxyethyl-                                                                  orange                                                        2,5-dimethyl-aniline                                 194  "            aniline N,N-diethyl-2,5-dimethoxy-                                                                      orange                                                        aniline                                              195  "            aniline N-ethyl-N-β-cyanethyl-2,5-                                                                 orange                                                        dimethoxy-aniline                                    196  "            aniline N-ethyl-N-β-hydroxyethyl-                                                                  orange                                                        2-methoxy-5-methyl-aniline                           197  "            aniline N-ethyl-N-β-cyanethyl-2-                                                                   orange                                                        methoxy-5-methyl-aniline                             198  "            aniline N,N-diethyl-N'-acetyl-m-                                                       yellowish-tinged red                                                           phenylenediamine                                     199  "            aniline N,N-diethyl-N'-propionyl-                                                                       yellowish-tinged red                                          m-phenylenediamine                                   200  "            aniline N-ethyl-N-β-hydroxyethyl-N'-                                                               yellowish-tinged red                                          acetyl-m-phenylenediamine                            201  "            aniline N-ethyl-N-β-acetoxyethyl-N'-                                                               yellowish-tinged red                                          acetyl-m-phenylenediamine                            202  "            aniline N,N-bis-(β-hydroxyethyl)-N'-                                                               yellowish-tinged red                                          acetyl-m-phenylenediamine                            203  "            aniline N,N-bis(β-acetoxyethyl)-N'-                                                                yellowish-tinged red                                          acetyl-m-phenylenediamine                            204  "            aniline N,N-bis-(β-methoxycarbonyloxy-                                                             yellowish-tinged red                                          ethyl)-N'-acetyl-m-phenylene-                                                  diamine                                              205  "            aniline N-ethyl-N-β-cyanethyl-N'-                                                                  yellowish-tinged red                                          acetyl-m-phenylenediamine                            206  "            aniline N-ethyl-N-β-chlorethyl-N'-                                                                 yellowish-tinged red                                          acetyl-m-phenylenediamine                            207  "            aniline N-ethyl-N-β-cyanethyl-N'-                                                                  yellowish-tinged red                                          propionyl-m-phenylenediamine                         208  "            aniline N-ethyl-N-β-cyanethyl-N'-                                                                  yellowish-tinged red                                          methoxycarbonyl-m-phenylene                                                    diamine                                              209  "            aniline N-ethyl-N-β-cyanethyl-N'-                                                                  yellowish-tinged red                                          benzenesulphonyl-m-phenylene-                                                  diamine                                              210  "            aniline N-ethyl-N-β-cyanethyl-N'-                                                                  yellowish-tinged red                                          methylsulphonyl-m-phenylene-                                                   diamine                                              211  "            aniline N,N-diethyl-2-methoxy-5-                                                                        red                                                           acetylamino-aniline                                  212  "            aniline N,N-bis(β-acetoxyethyl)-2-                                                                 red                                                           methoxy-5-acetylamino-                                                         aniline                                              213  "            aniline N,N-bis-(β-methoxycarbonyloxy-                                                             red                                                           ethyl)-2-methoxy-5-acetyl-                                                     amino-aniline                                        214  "            aniline N,N-bis-(β-methoxy-                                                                        red                                                           carbonyloxyethyl)-2-ethoxy-                                                    5-acetylamino-aniline                                215  "            aniline N-ethyl-N-β-cyanethyl-2-                                                                   red                                                           methoxy-5-acetylamino-aniline                        216  "            aniline N-β-acetoxyethyl-N-β-                                                                 red                                                           cyanethyl-2-methoxy-5-                                                         acetylamino-aniline                                  217  "            m-toluidine                                                                            N,N-diethylaniline                                                                              orange                              218  "            m-toluidine                                                                            N-ethyl-N-n-butyl-aniline                                                                       orange                              219  "            m-toluidine                                                                            N-ethyl-N-β-chlorethyl-                                                                    orange                                                        aniline                                              220  "            m-toluidine                                                                            N-n-butyl-N-β-cyanethyl-                                                                   orange                                                        aniline                                              221  "            m-toluidine                                                                            N-ethyl-N-β-hydroxyethyl-                                                                  orange                                                        aniline                                              222  "            m-toluidine                                                                            N-ethyl-N-β-acetoxyethyl-                                                                  orange                                                        aniline                                              223  "            m-toluidine                                                                            N-ethyl-N-β-methoxy-                                                                       orange                                                        carbonyloxyethyl-aniline                             224  "            m-toluidine                                                                            N,N-bis-(β-hydroxyethyl)-                                                                  orange                                                        aniline                                              225  "            m-toluidine                                                                            N,N-bis-(β-acetoxyethyl)-                                                                  orange                                                        aniline                                              226  "            m-toluidine                                                                            N,N-bis-(β-methoxycarbonyloxy-                                                             orange                                                        ethyl)-aniline                                       227  "            m-toluidine                                                                            N,N-bis-(β,γ-dihydroxy-                                                              orange                                                        propyl)-aniline                                      228  "            m-toluidine                                                                            N,N-bis(β-chlorethyl)-                                                                     orange                                                        aniline                                              229  "            m-toluidine                                                                            N-ethyl-N-β-carbomethoxy-                                                                  orange                                                        ethyl-aniline                                        230  "            m-toluidine                                                                            N-β-chlorethyl-N-β-methoxy-                                                           orange                                                        carbonyloxyethyl-aniline                             231  "            m-toluidine                                                                            N-β-chlorethyl-N-β-cyanethyl-                                                         orange                                                        aniline                                              232  "            m-toluidine                                                                            N-β-acetoxyethyl-N-β-                                                                 orange                                                        cyanethyl-aniline                                    233  "            m-toluidine                                                                            N,N-diethyl-m-toluidine                                                                         orange                              234  "            m-toluidine                                                                            N,N-bis-(β-hydroxyethyl)-                                                                  orange                                                        m-toluidine                                          235  "            m-toluidine                                                                            N,N-bis-(β-acetoxyethyl)-                                                                  orange                                                        m-toluidine                                          236  "            m-toluidine                                                                            N,N-bis-(β-methoxycarbonyloxy-                                                             orange                                                        ethyl)-m-toluidine                                   237  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-m-                                                                   orange                                                        toluidine                                            238  "            m-toluidine                                                                            N-ethyl-N-β-chlorethyl-m-                                                                  orange                                                        toluidine                                            239  "            m-toluidine                                                                            N-ethyl-N-β-hydroxyethyl-                                                                  orange                                                        m-toluidine                                          240  "            m-toluidine                                                                            N-ethyl-N-β-acetoxyethyl-                                                                  orange                                                        m-toluidine                                          241  "            m-toluidine                                                                            N-ethyl-N-β-methoxycarbonyloxy-                                                            orange                                                        ethyl-m-toluidine                                    242  "            m-toluidine                                                                            N-n-butyl-N-β-methoxy-                                                                     orange                                                        carbonyloxyethyl-m-                                                            toluidine                                            243  "            m-toluidine                                                                            N-n-butyl-N-β-acetoxyethyl-                                                                orange                                                        m-toluidine                                          244  "            m-toluidine                                                                            N-β-chlorethyl-N-β-acetoxy-                                                           orange                                                        ethyl-m-toluidine                                    245  "            m-toluidine                                                                            N-β-cyanethyl-N-β-acetoxy-                                                            orange                                                        ethyl-m-toluidine                                    246  "            m-toluidine                                                                            N,N-bis-(β-chlorethyl)-m-                                                                  orange                                                        toluidine                                            247  "            m-toluidine                                                                            N,N-diethyl-3-ethyl-aniline                                                                     orange                              248  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-3-                                                                   orange                                                        ethyl-aniline                                        249  "            m-toluidine                                                                            N-ethyl-N-β-hydroxyethyl-3-                                                                orange                                                        ethyl-aniline                                        250  "            m-toluidine                                                                            N,N-diethyl-3-chlor-aniline                                                                     orange                              251  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-3-                                                                   orange                                                        chlor-aniline                                        252  "            m-toluidine                                                                            N-ethyl-N-β-chlorethyl-3-                                                                  orange                                                        chlor-aniline                                        253  "            m-toluidine                                                                            N-ethyl-N-β-acetoxyethyl-                                                                  orange                                                        3-chlor-aniline                                      254  "            m-toluidine                                                                            N,N-diethyl-3-brom-aniline                                                                      orange                              255  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-3-                                                                   orange                                                        brom-aniline                                         256  "            m-toluidine                                                                            N,N-diethyl-m-anisidine                                                                         orange                              257  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-m-                                                                   orange                                                        anisidine                                            258  "            m-toluidine                                                                            N,N-diethyl-2,5-dimethyl-                                                                       orange                                                        aniline                                              259  "            m-toluidine                                                                            N-ethyl-N-cyanethyl-2,5-                                                                        orange                                                        dimethyl-aniline                                     260  "            m-toluidine                                                                            N-ethyl-N-β-chlorethyl-2,5-                                                                orange                                                        dimethyl-aniline                                     261  "            m-toluidine                                                                            N,N-diethyl-o-toluidine                                                                         orange                              262  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-o-                                                                   orange                                                        toluidine                                            263  "            m-toluidine                                                                            N-ethyl-N-β-acetoxyethyl-                                                                  orange                                                        o-toluidine                                          264  "            m-toluidine                                                                            N,N-diethyl-2,5-dimethoxy-                                                                      orange                                                        aniline                                              265  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-2,5-                                                                 orange                                                        dimethoxy-aniline                                    266  "            m-toluidine                                                                            N-ethyl-N-β-hydroxyethyl-                                                                  orange                                                        2-methoxy-5-methyl-aniline                           267  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-2-                                                                   orange                                                        methoxy-5-methyl-aniline                             268  "            m-toluidine                                                                            N,N-diethyl-N'-acetyl-m-                                                                        red                                                           phenylenediamine                                     269  "            m-toluidine                                                                            N,N-diethyl-N'-propionyl-                                                                       red                                                           m-phenylenediamine                                   270  "            m-toluidine                                                                            N,N-diethyl-N'-methyl-                                                                          red                                                           sulphonyl-m-phenylenediamine                         271  "            m-toluidine                                                                            N,N-diethyl-N'-benzene-                                                                         red                                                           sulphonyl-m-phenylenediamine                         272  "            m-toluidine                                                                            N,N-diethyl-N'-methoxycarbonyl-                                                                 red                                                           m-phenylendiamine                                    273  "            m-toluidine                                                                            N-ethyl-N-β-hydroxyethyl-N'-                                                               red                                                           acetyl-m-phenylenediamine                            274  "            m-toluidine                                                                            N-ethyl-N-β-acetoxyethyl-N'-                                                               red                                                           acetyl-m-phenylenediamine                            275  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-N'-                                                                  red                                                           acetyl-m-phenylenediamine                            276  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-N'-                                                                  red                                                           propionyl-m-phenylenediamine                         277  "            m-toluidine                                                                            N,N-bis-(β-hydroxyethyl)-                                                                  red                                                           N'-acetyl-m-phenylenediamine                         278  "            m-toluidine                                                                            N,N-bis-(β-acetoxyethyl)-                                                                  red                                                           N'-acetyl-m-phenylenediamine                         279  "            m-toluidine                                                                            N,N-bis-(β-methoxycarbonyl-                                                                red                                                           oxyethyl)-N'-acetyl-m-                                                         phenylenediamine                                     280  "            m-toluidine                                                                            N-ethyl-N-β-chlorethyl-N'-                                                                 red                                                           acetyl-m-phenylenediamine                            281  "            m-toluidine                                                                            N-β-cyanethyl-N-β-hydroxy-                                                            red                                                           ethyl-N'-acetyl-m-phenylene-                                                   diamine                                              282  "            m-toluidine                                                                            N-β-cyanethyl-N-β-acetoxy-                                                            red                                                           ethyl-N'-acetyl-m-phenylene-                                                   diamine                                              283  "            m-toluidine                                                                            N,N-diethyl-2-methoxy-5-                                                                        bluish-tinged red                                             acetylamino-aniline                                  284  "            m-toluidine                                                                            N,N-bis-(β-hydroxyethyl-                                                                   bluish-tinged red                                             2-methoxy-5-acetylamino-                                                       aniline                                              285  "            m-toluidine                                                                            N,N-bis-(β-acetoxyethyl)-                                                                  bluish-tinged red                                             2-methoxy-5-acetylamino-                                                       aniline                                              286  "            m-toluidine                                                                            N,N-bis-(β-methoxycarbonyl-                                                                bluish-tinged red                                             oxyethyl)-2-methoxy-5-                                                         acetylamino-aniline                                  287  "            m-toluidine                                                                            N-ethyl-N-β-cyanethyl-2-                                                                   bluish-tinged red                                             methoxy-5-acetylamino-                                                         aniline                                              288  "            m-toluidine                                                                            N-β-hydroxyethyl-N-β-                                                                 bluish-tinged red                                             cyanethyl-2-methoxy-5-                                                         acetylamino-aniline                                  289  "            3-amino-4-                                                                             N,N-diethylaniline                                                                              reddish-tinged orange                                 methoxy-                                                                       toluene                                                      290  "            3-amino-4-                                                                             N-ethyl-N-β-cyanethyl-                                                                     reddish-tinged orange                                 methoxy-                                                                               aniline                                                                toluene                                                      291  "            3-amino-4-                                                                             N-ethyl-N-β-hydroxyethyl-                                                                  reddish-tinged orange                                 methoxy-                                                                               aniline                                                                toluene                                                      292  "            3-amino-4-                                                                             N-ethyl-N-β-cyanethyl-m-                                                                   reddish-tinged orange                                 methoxy-                                                                               toluidine                                                              toluene                                                      293  "            3-amino-4-                                                                             N-ethyl-N-β-cyanethyl-3-                                                                   reddish-tinged orange                                 methoxy-                                                                               chlor-aniline                                                          toluene                                                      294  "            3-amino-4-                                                                             N-ethyl-N-β-chlorethyl-m-                                                                  reddish-tinged orange                                 methoxy-                                                                               anisidine                                                              toluene                                                      295  "            3-amino-4-                                                                             N,N-diethyl-N'-acetyl-m-                                                                        bluish-tinged red                                     methoxy-                                                                               phenylenediamine                                                       toluene                                                      296  "            3-amino-4-                                                                             N-ethyl-N-β-hydroxyethyl-N'-                                                               bluish-tinged red                                     methoxy-                                                                               acetyl-m-phenylenediamine                                              toluene                                                      297  "            3-amino-4-                                                                             N-ethyl-N-β-cyanethyl-N'-                                                                  bluish-tinged red                                     methoxy-                                                                               acetyl-m-phenylenediamine                                              toluene                                                      298  "            3-amino-4-                                                                             N-ethyl-N-β-cyanethyl-2-                                                                   bluish-tinged red                                     methoxy-                                                                               methoxy-5-methyl-aniline                                               toluene                                                      299  "            3-amino-4-                                                                             N-ethyl-N-β-cyanethyl-2-                                                                   ruby                                                  methoxy-                                                                               methoxy-5-acetylamino-                                                 toluene aniline                                              300  "            3-amino-4-                                                                             N,N-bis-(β-hydroxyethyl)-                                                                  ruby                                                  methoxy-                                                                               2-methoxy-5-acetylamino-                                               toluene aniline                                              301  "            3-amino-4-                                                                             N,N-bis-(β-methoxycarbonyloxy-                                                             ruby                                                  methoxy-                                                                               ethyl)-2-methoxy-5-acetyl-                                             toluene amino-aniline                                        __________________________________________________________________________

If instead of the acid sulphuric acid ester of ethylene glycol-(4-aminophenyl)-ether, the acid sulphuric acid esters of ethylene glycol-(2-chlor-4-aminophenyl)-ether, ethylene glycol-(3-chlor-4-aminophenyl)-ether, ethylene glycol-(2,6-dichlor-4-aminophenyl)-ether, ethylene glycol-(2,3-dichlor-4-aminophenyl)-ether, ethylene glycol-(2,5-dichlor-4-aminophenyl)-ether, ethylene glycol-(3,5-dichlor-4-aminophenyl)-ether, ethylene glycol-(2,3,5-trichlor-4-aminophenyl)-ether, ethylene glycol-(2,3,6-trichlor-4-aminophenyl)-ether, ethylene glycol-(2,3,5,6-tetrachlor-4-aminophenyl)-ether, ethylene glycol-(2-brom-4-aminophenyl)-ether, ethylene glycol-(3-brom-4-aminophenyl)-ether, ethylene glycol-(2-methoxy-4-aminophenyl)-ether, ethylene glycol-(3-methoxy-4-aminophenyl)-ether, ethylene glycol-(2-ethoxy-4-aminophenyl)-ether, ethylene glycol-(3-methoxy-4-aminophenyl)-ether, ethylene glycol-(3-ethoxy-4-aminophenyl)-ether, ethylene glycol-(2-ethyl-4-aminophenyl)-ether, ethylene glycol-(3-ethyl-4-aminophenyl)-ether, ethylene glycol-(2-chloro-5-methoxy-4-aminophenyl)-ether, ethylene glycol-(2-methyl-4-aminophenyl)-ether or ethylene glycol-(3-methyl-4-aminophenyl)-ether are used as the starting component, aniline, m-toluidine, 3-amino-4-methoxy-toluene, 2-amino-toluene, 2-amino-toluene, 2-amino-ethylbenzene, 3-amino-ethylbenzene, 3-chloraniline, 3-bromaniline, 2-amino-anisole, 3-aminoanisole, 2-aminoethoxybenzene, 3-aminoethoxybenzene, 1-aminoethoxybenzene, 1-amino-2,3 -dimethylbenzene, 1-amino-2,5-dimethylbenzene, 1-amino-3,5-dimethylbenzene, 2-amino-4-methoxy-toluene, 2-amino-1,4-dimethoxybenzene, 2-amino-4-ethoxytoluene, 2-amino-1,4-diethoxybenzene or α-naphthylamine are used as the middle component, and the end components indicated in the Tables are used as the end components, dyestuffs which dye polyamide in orange, red and ruby shades are again obtained.

Instead of the acid sulphuric acid ester of ethylene glycol, the acid sulphuric acid esters of trimethylene glycol or propylene glycol can also be used. 

I claim:
 1. Disazo dyestuff of the formula ##STR37## in which R'₁ is chlorine or methyl;R'₂ is hydrogen, chlorine, methyl, or methoxy; R'₃ is hydrogen or methoxy; R'₄ is hydrogen, chlorine, methyl, formylamino, acetylamino, hydroxyacetylamino, benzoylamino, methoxycarbonylamino, ethoxycarbonylamino, benzenesulfonylamino, toluenesulfonylamino, methylsulfonylamino, or ethylsulfonylamino; R'₅ is hydrogen, methyl, or methoxy; and m is a number from 0 to
 2. 2. Disazo dyestuff of the formula ##STR38## 